Acetic Acid → HCID 54444024, compound

HRID 1440715Notes

Reaction equation

HRID 1440715 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)=[O:3].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]=O.N1CCCCC1.C(O)(=O)C>C(OCC)(=O)C.C(O)C>[CH3:15][O:14][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH:1]=[CH:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=2)[CH:9]=[C:8]([O:10][CH3:11])[C:7]=1[O:12][CH3:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 142732-PyridinecarboxaldehydeHCID 143453',4',5'-Trimethoxyacetophenone

Product 1

HCID 54444024HCID 54444024, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 3,4,5-trimethoxyacetophenone (5.25 g, 25 mmol), 2-pyridinecarboxaldehyde (2 .35 mL, 25 mmol), piperidine (4.93 mL, 50 mmol), acetic acid (2.8 6 mL, 50 mmol) and ethanol (25 mL). Heat at reflux for 6 hour s, passing the distillate through a column of 3 Å molecular sieves (25 g). Dilute with ethyl acetate (600 mL), wash wit h saturated sodium hydrogen carbonate, then water, then saturated sodium chloride. Dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (70% ethyl acetate/hexane). Recrystallize (methylene chloride/ethyl ether/hexane) to yield the title compound; mp 94°-5° C.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 6 hour s
  3. washwash wit h saturated sodium hydrogen carbonate
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify by silica gel chromatography (70% ethyl acetate/hexane)
  7. customRecrystallize (methylene chloride/ethyl ether/hexane)

Sources & evidence

ORD record
ord-a436b6c76fd64271a732a646431b0ff7
Source dataset
uspto-grants-1996_03
Patent number
US05500429

Reaction notes

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